반응 #11194

반응 방정식

Mesylate

2-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)ethyl methanesulfonate

thiophenol

triethylamine

→

carbazole

수율 27.0%

4-(2-Chlorophenyl)-9-hydroxy-6-[2-(phenylsulfanyl)ethyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

수율 27.0%

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   추출by extracted of the compound with with ethyl acetate
3. 3
   기타The organic layer was dried
4. 4
   기타the drying agent was removed
5. 5
   농축the solution was concentrated to dryness
6. 6
   기타The organic layer was dried
7. 7
   기타the drying agent was removed
8. 8
   농축the solution was concentrated to dryness

실험 절차

Mesylate (229) (55 mg, 0.11 mmol) prepared as decribed in example 171 was reacted with excess thiophenol (0.10 mL) according to the procedure described in example 179, except that triethylamine (2.0 mL) was added and the reaction was heated at 110° C. for 4 days. Addition of water was followed by extracted of the compound with with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness followed by chromatography on silica eluting with ethyl acetate/hexane (1:4 to 1:1) to give carbazole (242) (16 mg, 27%) as an orange powder, mp 262–264° C. 1H NMR δ [(CD3)2SO] 11.04 (br s, 1H), 9.37 (br s, 1H), 8.34 (d, J=2.5 Hz, 1H), 7.58 (m, 1H), 7.46 (m, 5H), 7.19 (m, 2H), 7.12 (m, 3H), 7.05 (m, 1H), 4.66 (t, J=6.4 Hz, 2H), 3.46 (t, J=6.4 Hz, 2H). Found: C, 63.64; H, 4.09; N, 4.98. C28H19ClN2O3S.1¾H2O requires: C, 63.39; H, 4.28; N, 5.28.

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